Enantioselective N-acetylation of racemic secondary alkyl amines with chiral 2-acetylamino-2′-diacetylamino-1,1′-binaphthyl

Synlett

Volumn , Issue 7, 1998, Pages 725-726

  Kondo, Kazuhiro ^a   Kurosaki, Takahiro ^a   Murakami, Yasuoki ^a  

^a TOHO UNIVERSITY   (Japan)

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[No Author keywords available]

Indexed keywords

EID: 0002357999     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1783     Document Type: Article

References (29)

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21. Kondo, K.; Murakami, Y. Chem. Pharm. Bull, in press.
22. Chiral 1,1′-binaphthyl-2,2′-diamine (1) was purchased from Aldrich.
23. 2O in pyridine.
24. No acetylation of amine 4 occurred with tetraacetyl derivative 11, which was prepared as shown in Scheme 2. (Chemical Equation Presented)
25. Another derivative 12 gave lower ee as shown in Scheme 3. (Chemical Equation Presented)
26. 3CN (30%, 28% ee).
27. Miyano, S.; Nawa, M.; Mori, A.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 2177.
28. The enantiomeric excesses of N-acetylamines were determined by HPLC analysis using chiral phase column (For 7, 10: DAICEL CHIRALCEL OD; For 6: DAICEL CHIRALCEL OB; For 8,9: DAICEL CHIRALCEL OJ). The absolute configurations of N-acetylamines were determined by comparison with the commercially available acetylated amines of known configuration.
29. 3: C, 76.08; H, 5.40; N, 6.82. Found: C, 76.20; H, 5.25; N, 6.88.